Three Very Memorable Holidays
by Hypnotoad76
Summary: Jeff and Annie go out on their first three dates, which happen to fall on three already well known days.


**Date Number One**

This was not how he had expected the day to go.

That thought briefly ran through Jeff's head as his back was pushed even harder against the couch by Annie. She was straddling his waist, grinding her crotch against his denim crushing erection as their lips furiously crashed against each other. He grabbed hold of her waist as he pulled her closer, still unable to believe that this was actually happening.

It all started when Annie came over that afternoon for their 'Non Christmas Themed Movies Set on Christmas Marathon'. Originally Abed was supposed to join them, but at the last minute he found out there was a Christmas day screening of _Kick Puncher Saves Christmas_ and went to that, leaving just the two of them to watch the movies together. Nothing happened as they watched _Gremlins_ and_ Die Hard_. But then they put on _Black Christmas_, and things slowly progressed from there. Annie wasn't a huge fan of horror movies (horror books she loved, but not movies), and found herself moving closer and closer to Jeff as the movie went on. She took hold of his hand during each of the disturbing phone calls, and gripped his whole arm when the girl went up to the attic and was suffocated with a plastic bag. By the time the infamous 'eye scene' happened she buried her face against him in fright while he held onto her tightly to comfort her. Somehow this led to her kissing him, and things quickly progressed from there.

Jeff couldn't believe that this was happening. After everything that had happened between them, they were going at it like lust starved lovers. After denying his feelings for so long, and the back and forth emotional dance they'd shared, in the end it suddenly seemed so easy. Like he had done this a million times before.

It was that thought (realizing he already had done this with just about every woman he'd been with) that caused him to suddenly pull his mouth from hers. "Annie, wait."

"What?" she said breathlessly as he practically pushed her off him.

"We can't do this." He quickly amended his statement at seeing the hurt and angry look on her face. "No wait, I didn't mean it like that." To prove his point he leaned in to kiss her (just enough to let her know he still wanted her) before reluctantly pulling back. "I meant to say that I don't want to treat you like I treat every woman I've been with, where I just have sex with them right away. You deserve more than that.

She smiled brightly as he got up and offered her his hand. "So, what's the plan," she said as he pulled her to her feet.

"I'm taking you out to dinner, on a real, no-other-way-to-interpret-it date."

XXXXXXXXXXXX

"TABLE SIX WANTS ANOTHER SHRIMP PLATTER DELIGHT!" a waiter yelled as he walked past Annie and Jeff's table, causing the two of them to rub their ears.

After deciding to go out for dinner, Annie and Jeff had the daunting task of finding a place that was open on Christmas. It turned out the only places that were open were Chinese restaurants. They tried four places that were completely booked before finding The Lucky Duck, a questionable looking eatery in a decrepit run down strip mall.

"So as far as first dates go, this wasn't what I had in mind."

"Jeff, it's fine," Annie said as she cautiously inspected a piece of her orange chicken (which looked more like sesame chicken that had been nuked).

"No it's not. You deserve to eat at a fancy restaurant. Not a place that looks like it only passed the health inspection because the owner bribed the inspector," Jeff said as he picked out a black specked ice cube from his plastic cup.

"Jeff." He looked over at her as she smiled warmly at him. "This might not be the most ideal place to have our first date. But the fact that you wanted to take me out before we slept together, that means a lot to me." Her smile grew more mischievous as she rubbed her foot against his leg. "And I'm going to show you how much it means to me before the night is over."

"Then let's get out of here quickly," Jeff said as he took a bite of his meal and reluctantly swallowed it. "Yeah, this is awful. You know what would have been great? If we could have found an open deli. We must have passed by six delis and all of them were closed. That would be a gold mine for everyone who doesn't celebrate Christmas or doesn't care about the holidays."

"That would have been great if we had found an open deli." Annie said thoughtfully. "I'd rather have a roast beef sandwich then this stuff. I remember after the divorce my mom would always get egg rolls and chow mein from this place near my house every Christmas. I think it was her way of purposely being as culturally clichéd as possible, but the food wasn't bad. What about you? Did your mom cook on Christmas?"

"No," Jeff responded with a laugh. "My mom always got catering from this Italian restaurant two days before Christmas and then would just reheat it. I didn't know what fresh eggplant parmesan tasted like until after I moved out."

Annie giggled as she put a forkful of her food into her mouth. Her eyes then suddenly watered as she spit the food into her napkin and quickly gulped down her water.

"Are you okay? What happened?"

"It was really spicy," Annie said as she inspected her napkin. "I think it was a chili pepper."

"Why would they use chili peppers at a Chinese restaurant?"

"I don't know," Annie groaned as she carefully combed through her meal to make sure there weren't anymore surprises in it.

As they continued ate their questionable dinners Annie tried to focus on the good things. A cynical person might think this first date was a bad omen. But Annie was determined to keep see the good in it. Besides, she thought, it can only get better from here.

XXXXXXXXXXXX

Annie threw her head back in ecstasy before her moan morphed into a cry of pain as she hit her head on the backseat window. "Ow!"

"You ok?" Jeff asked.

"Yeah, I'm fine," she said disgruntledly. "Can you move up a little?"

"I have barely any room as it is," Jeff said as he scrunched his body to try and get more comfortable, inadvertently kicking the window and narrowly missing Annie with his feet.

By the time they left the restaurant Annie was feeling very affectionate, and quite turned on. Wanting to be daring she suggested they didn't have to wait until they got to Jeff's place before having sex. So Jeff pulled the car into the deserted back parking behind the strip mall before they climbed in the back seat to consummate their relationship. It turned out car sex was one of those 'the idea is better than the act' things. There was hardly any room to move, and they both kept hitting the doors.

"I thought you've done this before," Annie hissed as her neck and shoulders again hit the door.

"Yeah, in my car. Your car's a lot smaller."

"Well you insisted we take my car because yours was just waxed and it's supposed to snow later," she said in an annoyed voice. "Maybe it'll work better if you're on top." She moved her body against the door when her hand hit the door latch and accidently opened it. She screamed as she fell back, falling out of the car and hitting her butt hard against the pavement. "Ow!"

"Holy crap. Are you all right?"

"I'm fine," she said sternly. Annie quickly scrambled back in the car to avoid anyone seeing her naked and gingerly felt her sore butt and hips. "That's it, I'm done. I just want to go home."

"Yeah, ok," Jeff said. They both put their clothes back on before getting in the driver and passenger seats and driving off.

As they made their way home Annie thought about how disastrous things had gone. After all their build up, _this_ was how their first date went. Maybe she was wrong and it really was an omen. Maybe they really weren't meant to be together.

Jeff looked over at Annie as she drove, seeing what he referred to as her 'sad thinking face'. She couldn't be thinking anything good after their disastrous date. He thought he would really impress her by insisting they go out before having sex. And now it seemed the smarter choice would have been for them to just do it on the couch.

_Maybe it's better that this happened now_, he thought. _Now we know this would never have worked and can finally move on._

Except strangely, Jeff didn't want to move on. The mere fact that Jeff insisted they go out before sleeping together was revolutionary. He had never remotely done that before. Every other woman he had been with he either slept with them right off the bat, or went out with them for the sole goal of it leading to sex. But with Annie, he wanted more. And he was damned if he was going to have _this_ be her impression of dating Jeff Winger.

Now he just had to figure out a way of giving her what she deserved.

XXXXXXXXXXXX

**Date Number Two**

"Bye. Thanks again for coming," Annie happily said as Shirley and her boys left. She grinned widely as she closed the apartment door. This had been a fun birthday. Even though they just had a simple party at her place, it was nice to see everyone. They sang happy birthday and ate a homemade cake Shirley had personally made. She had gotten some real good gifts (her favorite turned out to come from Pierce, who got her a new lap top computer). And she had a lot of fun playing Wii bowling, even if after four games she still couldn't beat Abed. So all in all it was a good day.

She started gathering up some stray wrapping paper when she noticed Jeff was still here. "Did you forget something?"

"No. But I did want to show you something."

"What?"

"You'll have to come with me. Please?"

She looked at him questionably before nodding her head yes. "All right." She threw out the paper in her hands and grabbed her coat before yelling to Troy and Abed, "I'm going out with Jeff."

"Okay," Troy yelled as the two of them continued to play Wii bowling.

XXXXXXXXXXXX

"All right," Jeff said as they walked into his apartment. "Just wait here for a little bit while I do something. Trust me, it'll be worth it."

Annie watched Jeff curiously as he grabbed a large paper bag from his room and another from the refrigerator before walking out of the apartment. She sat down on the couch, wondering what was going to happen. He had been very antsy and fidgety during the party, and refused to give her a straight answer during the whole car ride over. She very much wanted to know what was causing Jeff to be so evasive.

She waited fifteen minutes before Jeff came back in. "If you'll put on your coat and follow me."

"Jeff, what's going on?"

"Annie, I promise you'll love this. Trust me."

She sighed heavily before putting on her coat and following Jeff. They took the elevator to the top floor and walked over to a door. "Close your eyes." Annie looked at Jeff before closing them. She listened carefully as she heard the door open and then felt Jeff take her hand and led her through it, where she instantly realized they were outside. She slowly walked as Jeff guided her before she heard him say, "Okay, open."

Annie opened her eyes, seeing they were in a greenhouse on the roof of his building. She let out a gasp when she saw what Jeff had done. Several strands of white lights were strung around the glass walls. Near the wall which gave them a view of the night sky was a blanket and two covered plates of food.

She tried to discreetly wipe the tears that were forming as Jeff led her over to their picnic. He lit a few candles before uncovering her plate. Annie let out a laugh when she saw what it was: a roast beef sandwich with a bag of chips. "You said you wished you could have had roast beef on Christmas. So…"

Annie inched over to Jeff and threw her arms around him before kissing him deeply. "Jeff, this is great. I can't believe you did this."

"Well, after that terrible first date, I couldn't leave things like that. So this is kind of a do over." He pulled out a bottle of wine and two glasses from a bag before pouring them a glass each. "To…realizing things you should have seen all along."

"To realizing things," Annie said happily as they clinked their glasses together and took a sip. As they talked and ate their food Annie felt a warm bubbling feeling in her stomach. She had had very real doubts regarding them after how their first date went. But seeing Jeff go to this much effort to make up for it made her believe that this might work. That maybe they could make it work.

Jeff smiled as he listened to Annie talk about her birthday celebration. He was glad he came up with this way of showing her that the two of them going out wouldn't be a complete disaster. And this wasn't even the only surprise he had in store.

XXXXXXXXXXXX

**Date Number Three**

Jeff knocked on Apartment 303's door, waiting only a few moments before it opened. "Wow," he said as he took in Annie's attire. Annie was wearing a spaghetti strapped purple cocktail dress, along with heels and silver earrings. "You look gorgeous."

"Thank you. You're looking good yourself," she said as she took in Jeff's stylish dark grey suit. "This isn't too much is it? I know you said to get dressed up, but-."

"No, that's great. And it's New Year's Eve. Everyone is going to be dressed up. So, shall we?"

XXXXXXXXXXXX

Like their previous date, Jeff wasn't saying anything to her, but this time Annie didn't mind. After how things went the last time, she had faith that tonight would also be amazing. They drove for an hour and a half, the afternoon sky steadily growing darker. They arrived in Denver just as the last rays of light of 2012 left the sky. Annie looked out the window at the streets, seeing people walk to various restaurants and city hot spots to celebrate New Year's Eve.

"Here we are," Jeff said as he pulled in front of a fancy looking restaurant. They got out of the car as a valet came over to them. "Good evening sir, how are you?"

"Fine." Jeff took his car key off the key ring and gave it to the valet while slipping a twenty in his pocket. "This car means a lot to me."

"Don't worry, she'll be returned to you just as you left her. Trust me," the guy said as he gave Jeff a ticket stub before driving away.

"I really hope he doesn't try to reenact _Ferris Bueller's Day Off_," Jeff exclaimed. He shook his head before offering his arm to Annie. "Milady."

"Milord," Annie replied with a smile, happy to again say the pet names that had been lost recently. She took his arm and they walked into the restaurant.

"Good evening and welcome to Esperienza," the host said. "What name is your reservation under?"

"It's actually not listed. But if you'll just call Mr. Velensia and tell him Jeff Winger is here, it'll all be straightened out," Jeff said confidently.

"Sir, this is New Year's Eve, one of our busiest nights. Our tables book weeks, sometimes months in advance for our New Year's celebration. I don't have time to play games-."

"Just tell him Jeff Winger is here."

The host glared at Jeff as he whispered into his walkie. He listened to the speaker on the other end as his face morphed from annoyed to surprise. He put the walkie down, looking at Jeff and Annie apologetically. "If you'll just wait here for a few moments."

"Jeff, what's going on?" Annie asked.

"Aw, Jeff!" She looked over as a large man with a pencil thin mustache walked over to them. "So good to see you. So Good. You doing well?"

"I am Paulie."

"Good to hear, good to hear. And is this the special lady you said would be joining you?"

"Yes she is. This is Annie."

"Annie, I am Paulie Velensia, proud owner of Esperienza," he said as he kissed her hand. "And any woman who is with Jeff Winger is a very lucky woman indeed. If you two will follow me."

Annie marveled at the stylish décor as she followed Jeff and Paulie through the crowded restaurant. They maneuvered through the tables until they came to a private booth in a secluded spot near the back. "Here you are, best seat in the house." Paulie smiled as they sat down and he handed them menus. "Now tonight, Paulie is your personal overseer for the evening. Anything you need, anything at all, do not hesitate to ask. Enjoy." With that he clapped his hands together before going on his way.

Annie watched him go in shock before looking at Jeff. "Jeff, how is this possible? How did you do this?"

"I was his lawyer in a drunk driving case a few years ago, and he owed me a favor." Jeff reached over and put his hand above hers. "I told you that you deserved to have a date at a fancy restaurant."

"Jeff…I just don't know what to say. Between the picnic and this…." She paused to gather herself before letting out a giggle. "You never cease to amaze me."

"Thanks. Though to be fair, you're the real amazing one here. I didn't think I had any of this in me. But with you, you make me want to try. And it's not even that bad of a thing."

The evening went on with an almost magical vibe to it. They ate several courses of extremely fine Italian cooking, with Paulie accompanying the wait staff to tell them he personally made them dishes that weren't even on the menu. They talked for hours, feeling completely at ease and never experiencing a lull in the conversation. Once they finished their desert they went upstairs to the dance floor, where a live band was playing. Jeff wasn't the most skilled dancer, but Annie didn't care how he looked out there. She was so enjoying herself she didn't even mind when he occasionally stepped on her toes. The fact that he held her close to him during the slow songs more than made up for it.

Just before midnight the TV's in the room were switched to Time Square and everyone was handed glasses of champagne. They all looked at Paulie as he stood on the band platform. "Ok everyone, get ready. Ten, nine, eight, seven, six, five, four, three, two, one, HAPPY NEW YEAR!"

While most people in the room cheered and blow noise makers, Jeff pulled Annie into him as he gave her a kiss that almost made her knees buckle. "Happy New Year babe."

"Happy New Year Jeff."

He kissed her again before smiling at her. "There is one more thing. And if you don't want to I'm perfectly fine with going back to Greendale. But I got a hotel room if you're interested."

"Oh, I'm_ very_ interested," she said with a sexy grin. "Although let's wait until we actually get to the room this time."


End file.
